US4195177A - Hydroxyalkyl-etherified glycolipid ester - Google Patents

Hydroxyalkyl-etherified glycolipid ester Download PDF

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Publication number
US4195177A
US4195177A US05/962,664 US96266478A US4195177A US 4195177 A US4195177 A US 4195177A US 96266478 A US96266478 A US 96266478A US 4195177 A US4195177 A US 4195177A
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United States
Prior art keywords
ester
acid
hydroxyalkyl
glycolipid
saturated
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Expired - Lifetime
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US05/962,664
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English (en)
Inventor
Shigeo Inoue
Yoshiharu Kimura
Manzo Kinta
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Kao Corp
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Kao Soap Co Ltd
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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • C07H15/10—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical containing unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
    • C07H3/04—Disaccharides
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/12—Disaccharides

Definitions

  • This invention relates to a novel wax-like substance possessing surface activity characteristics, and to a process for producing the same. More particularly, the invention relates to hydroxyalkyl-etherified glycolipid esters represented by formula (I), ##STR3## wherein R 1 represents a methyl group or a hydrogen atom, R 2 represents a saturated or unsaturated hydrocarbon group having 11 to 15 carbon atoms when R 1 is a methyl group and R 2 represents a saturated of unsaturated hydrocarbon group having 12 to 16 carbon atoms when R 1 is a hydrogen atom, R 3 represents a saturated or unsaturated hydrocarbon group having 1 to 20 carbon atoms, A represents --CH 2 --CH 2 --O-- or ##STR4## and a,b,c,d,e,f and g represent integers whose sum ranges from 1 to 60, and represented by formula (II), ##STR5## wherein R 1 , R 2 and A are the same as defined above, and s,t,u, v,w,x,y,
  • the esters have been widely used as glazing materials and oily substances for leather, cosmetics and ointments, lubricants for fibers, machinery, stationery, printing, rust inhibition and insulation and have been used in metal processing.
  • formulation technique of a high degree is required for emulsification of wax because the wax characteristics depend directly upon such formulation technique.
  • Wool wax which is known under the name of lanolin, includes in its structure a peculiar ester bond formed between the long-chain branched fatty acid and the long-chain branched aliphatic alcohol or steroid alcohol, it is a wax substance having both an excellent wax-like property and a proper emulsifying ability.
  • wool wax is a mysterious naturally occurring compound and does not find wide applicability partly because its combination with other materials require highly advanced techniques and partly because the amounts used are limited because of its peculiar animal smell.
  • glycolipid ester of the formula (III) lacks heat stability at high temperatures and viscosity. The reason is that the hydroxy group of the sugar moiety of this compound exists in a free form, thereby resulting in reduced adhesiveness, lubricity, flexibility and plasticity.
  • the compounds of the formulae (I) and (II) are produced according to the present invention, as shown in the following reaction scheme, by reacting a glycolipid ester of the formula (III) or glycolipid of the formula (IV) with an alkylene oxide in the presence of an alkali catalyst.
  • R 1 , R 2 and R 3 are the same as defined above.
  • R 1 and R 2 are the same as defined above.
  • the starting material of formula (III) or a glycolipid ester can be produced by a method found by the present inventors.
  • Sophorolipid is subjected to methanolysis and methylation reactions by reaction with methanol in an acid to produce a glycolipid methyl ester which is further converted into the compound of formula (III) by reacting the glycolipid methyl ester with an alcohol of the formula, ROH, wherein R is a saturated or unsaturated hydrocarbon group having 2 to 20 carbon atoms, and by subject the resulting reaction mixture to an ester interchange reaction.
  • the starting material of formula (IV) or glycolipid is produced by hydrolyzing the glycolipid methyl ester.
  • Suitable alkylene oxides which are useful in the invention include ethylene oxide and propylene oxide.
  • the compounds of formulas (III) and (IV) readily react with alkylene oxides under the conditions applicable to a normal addition reaction.
  • an alkali catalyst is preferably used because glucoside bonds of the disaccharide may be cleaved by acid.
  • Suitable alkali catalysts which are useful in the invention include sodium metal, potassium metal, sodium hydroxide, potassium hydroxide, sodium alcoholate, potassium alcoholate and the like.
  • the alkali catalyst is used preferably in an amount of from 0.2 to 1.0 in terms of its weight percent to the glycolipid or glycolipid ester.
  • the reaction is carried out preferably at a temperature ranging from 70° to 120° C., especially from 100° to 120° C.
  • the catalyst may be used singly or in combination.
  • the reaction progress can be observed by measuring the pressure in the reactor or by quantitatively analyzing the reaction products so that an adduct having any predetermined addition number can be produced.
  • the hydroxyalkyl-etherified glycolipid ester thus obtained according to the invention does not undergo any structural degeneration or deterioration in a preservation test at 250° C. for 48 hours because the hydroxy groups in the sugar structure are combined with the hydroxyalkyl groups through the stable ether bonds.
  • a variety of substances having both wax-like and hydrophilic properties and surface activities suitable for any desired purposes of application can be produced by varying the species of the glycolipid ester and addition mole number since any addition mole number of the alkylene oxide may be specified.
  • EO denotes ethylene oxide
  • PO denotes propylene oxide in Table 1.
  • the present compound of formula (I) possesses an extremely excellent effect when applied as an oil for cosmetics and leather, and as a softening lubricant for fiber.
  • the compound serves as an emulsifying agent, and it imparts elasticity and lubricity to the skin because of its affinity to the skin.
  • reaction solution was neutralized with potassium hydroxide and filtered with filter paper.
  • the filtrate was placed in a round bottom flask equipped with a Liebig condenser, and methanol and methyl acetate were distilled off to give 48 g of a brown paste mixture which contained 94% of [(2'-O- ⁇ -D-glucopyranosyl- ⁇ -D-glucopyranosyl)oxy]-alkane acid and -alkene acid methyl ester, and polypropyleneglycol.
  • This mixture was purified by column chromatography on silica gel, and there were obtained pure [(2'-O- ⁇ -D-glucopyranosyl- ⁇ -D-glucopyranosyl)oxy]-alkane acid and -alkene acid methyl esters.
  • Ester value 87 This product was degraded in a 5 N hydrochloric acid-methanol solution to give 2 moles of a methyl glycoside and 1 mole of a hydroxyfatty acid methyl ester, which was quantitatively analyzed by gas chromatography.
  • a 100 g amount of the mixture of [(2'-O- ⁇ -D-glucopyranosyl- ⁇ -D-glucopyranosyl)oxy]-alkane acid and -alkene acid methyl esters, and polypropyleneglycol obtained in Reference Example 1 was placed in an autoclave together with 0.25 g of potassium hydroxide, and the mixture was reacted at 100°-120° C. for 6 hours with an amount of ethylene oxide gas corresponding to the addition mole number shown in Table 2 being passed into the reaction mass. After the completion of the reaction, the mixture was neutralized with phosphoric acid, and the formed potassium phosphate was filtered off under increased pressure to obtain a crude product.
  • This product was purified by column chromatography on silica gel to remove the ethylene oxide adduct of polypropylene glycol to afford polyoxyethylene[2'-O- ⁇ -D-glucopyranosyl- ⁇ -D-glucopyranosyl)oxy]-alkane acid and -alkene acid methyl esters as a pale yellow paste.
  • a 100 g amount of the mixture of [(2'-O- ⁇ -D-glucopyranosyl- ⁇ -D-glucopyranosyl)oxy]-alkane acid and -alkene acid methyl esters, and polypropyleneglycol obtained in Reference Example 1 was placed in an autoclave together with 0.25 g of potassium hydride, and the mixture was reacted at 100°-120° C. for 6 hours with an amount of a propylene oxide gas corresponding to the addition mole number shown in Table 4 being passed into the reaction mass. After the completion of the reaction, the mixture was neutralized with phosphoric acid and filtered under increased pressure to obtain a crude product as a brown paste.
  • This product was purified by column chromatography on silica gel to afford polypropylene[(2'-O- ⁇ -D-glucopyranosyl- ⁇ -D-glucopyranosyl)oxy]-alkane acid and -alkene acid methyl esters as a pale yellow paste.
  • the filtrate was placed in a 500 ml three-necked flask equipped with a Liebig condenser and was evaporated under normal pressure to remove methanol and ethanol. Thereafter, water was distilled off under reduced pressure to yield [(2'-O- ⁇ -D-glucopyranosyl- ⁇ -D-glucopyranosyl)oxy]-alkane acid and -alkene acid.
  • a 20 g amount of a glycolipid methyl ester-polypropylene glycol mixture was placed in an autoclave, and to this mixture were added 4.2 g of actyl alcohol and 5 g of methanol to obtain a homogeneous solution, then 0.1 g of sodium methylate.
  • the greater part of methanol was distilled off at 70° C., and an ester interchange reaction was carried out while methanol which formed was distilled off with stirring under a reduced pressure of 250 mmHg.
  • the reaction progress was observed by gas chromatography under the following conditions: glass column; 3% silicon JXR-Chromsolve W having 60 ⁇ 80 meshes; inside diameter 3 mm; height 1 m; column oven temperature of 250° C. ⁇ 350° C; pressure by helium gas of 0.6 kg/cm 2 ; and hydrogen flame detecter as a detector.
  • the reaction state was measured from the peak area ratio of the glucolipid methyl ester and glycolipid octyl ester with a sample picked up from the reaction solution and trimethyl-sililated with a trimethylsililating agent.
  • the reaction was regarded as having been completed when the peak of the glycolipid methyl ester disappeared.
  • the mixture was reacted at 100°-120° C. for 6 hours with an ethylene oxide gas in an amount specified in Table 8 being passed into the reaction mass, to obtain an ethylene oxide adduct.
  • the amount of ethylene oxide was varied according to the specified addition mole number as shown in Table 8.
  • the mixture was neutralized with phosphoric acid, and the formed sodium phosphate was filtered off under increased pressure.
  • a 5 g amount of the sample was purified by column chromatography on 500 g of silica gel (chloroform-methanol; gradient elution) to obtain polyoxyethylene [(2'-O- ⁇ -D-glucopyranosyl- ⁇ -D-glucopyranosyl)oxy]-alkane acid and -alkene acid octyl ester fractions which amounted to 91 to 94% by weight of the whole sample weight.
  • a 20 g amount of the mixture of glycolipid methyl ester-polypropylene glycol obtained in Reference Example 1 was placed in an autoclave, and to this mixture were added 8.9 g of oleyl alcohol, t g of methanol and then 0.1 g of sodium methylate.
  • the reaction conditions for ester interchange and ethylene oxide addition were the same as in Inventive Example 4. 21.0 g of an ethylene oxide gas was reacted with the mixture and an adduct was obtained having an average addition number of 15. 29.8 g of the ethylene oxide adduct thus obtained was neutralized with phosphoric acid, and the formed sodium phosphate was filtered off under increased pressure.
  • propylene oxide adduct was neutralized with phosphoric acid, and the formed sodium phosphate was filtered off under increased pressure.
  • 5 g of the sample was purified by column chromatography under the same conditions as in Inventive Example 4 to afford polyoxypropylene[(2'-O- ⁇ -D-glucopyranosyl- ⁇ -D-glucopyranosyl)oxy]-alkane acid and -alkene acid lauryl ester fractions which amounted to 90 to 93% by weight of the whole sample weight.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Molecular Biology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Microbiology (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Birds (AREA)
  • Dermatology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Saccharide Compounds (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Medicinal Preparation (AREA)
  • Cosmetics (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US05/962,664 1978-03-03 1978-11-21 Hydroxyalkyl-etherified glycolipid ester Expired - Lifetime US4195177A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP53/24306 1978-03-03
JP2430678A JPS55303A (en) 1978-03-03 1978-03-03 Hydroxyalkyl etherified glycolipid ester and its preparation

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EP (1) EP0005004B1 (es)
JP (1) JPS55303A (es)
DE (1) DE2964772D1 (es)
ES (1) ES477364A1 (es)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4309447A (en) * 1978-09-29 1982-01-05 Kao Soap Co., Ltd. Skin-protecting cosmetic composition
US4362720A (en) * 1977-04-14 1982-12-07 Chembiomed Ltd. Synthesis of 2-amino-2-deoxyglycoses and 2-amino-2-deoxyglycosides from glycals
US4870010A (en) * 1984-10-16 1989-09-26 Petroleum Fermentations N.V. Bioemulsified-containing personal core products for topical application to dermopathologic conditions of the skin and scalp
US4999195A (en) * 1984-10-16 1991-03-12 Emulsan Biotechnologies Inc. Personal care products containing bioemulsifiers
US5037969A (en) * 1986-07-03 1991-08-06 Takeda Chemical Industries, Ltd. Glycosyl derivatives and use thereof
US20070249542A1 (en) * 2003-03-24 2007-10-25 Gross Richard A Treatment and prophylaxis of sepsis and septic shock
US20100234320A1 (en) * 2009-03-11 2010-09-16 Bioamber Sas Emulsifying compositions based on alkyl polyglycosides and esters

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5428895A (en) * 1977-08-01 1979-03-03 Kao Corp Dehydration purification of fermentation products
GB2033895B (en) * 1978-09-22 1983-01-19 Kao Corp Hydroxypropyletherified glycolipid esters
JPS5547610A (en) * 1978-09-29 1980-04-04 Kao Corp Hair cosmetic
JPS6037087B2 (ja) * 1978-09-28 1985-08-24 花王株式会社 化粧料
JPS62113043A (ja) * 1985-11-12 1987-05-23 Toray Ind Inc 巻取ロ−ル状物の硬度測定装置
CA2086228C (en) * 1991-12-31 1998-09-22 Robert W. Humphreys Glycolipid surfactants and compositions containing them
US5358656A (en) * 1991-12-31 1994-10-25 Lever Brothers Company, Division Of Conopco, Inc. Compositions comprising glyceroglycolipids having an amine linkage as a surfactant or cosurfactant
ES2086677T3 (es) * 1991-12-31 1996-07-01 Unilever Nv Composiciones que contienen un gliceroglicolipido.
FR2997400B1 (fr) * 2012-10-29 2015-07-24 IFP Energies Nouvelles Procede de production de sophorose a partir de sophorolipides

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2652394A (en) * 1950-02-27 1953-09-15 Petrolite Corp Certain oxyalkylated derivatives of sucrose
US2927919A (en) * 1957-12-30 1960-03-08 Dow Chemical Co Ether-esters of sucrose
US3022335A (en) * 1955-03-30 1962-02-20 Wyandotte Chemicals Corp Surface active polyoxyalkylene compounds having a plurality of heteric polyoxypropylene-polyoxyethylene chains
US3305542A (en) * 1965-03-25 1967-02-21 Weyerhaeuser Co Polyethers of levoglucosan
US3442888A (en) * 1962-05-17 1969-05-06 Allied Chem Sucrose - glycerol - alkyleneoxide polyol compositions and process for preparing same
US3459733A (en) * 1964-10-15 1969-08-05 Mobil Oil Corp Monomeric polyesters of polyhydroxy compounds and process for preparing same
US3535307A (en) * 1964-01-02 1970-10-20 Jefferson Chem Co Inc High molecular weight polyether blocked polymers

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5428895A (en) * 1977-08-01 1979-03-03 Kao Corp Dehydration purification of fermentation products

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2652394A (en) * 1950-02-27 1953-09-15 Petrolite Corp Certain oxyalkylated derivatives of sucrose
US3022335A (en) * 1955-03-30 1962-02-20 Wyandotte Chemicals Corp Surface active polyoxyalkylene compounds having a plurality of heteric polyoxypropylene-polyoxyethylene chains
US2927919A (en) * 1957-12-30 1960-03-08 Dow Chemical Co Ether-esters of sucrose
US3442888A (en) * 1962-05-17 1969-05-06 Allied Chem Sucrose - glycerol - alkyleneoxide polyol compositions and process for preparing same
US3535307A (en) * 1964-01-02 1970-10-20 Jefferson Chem Co Inc High molecular weight polyether blocked polymers
US3459733A (en) * 1964-10-15 1969-08-05 Mobil Oil Corp Monomeric polyesters of polyhydroxy compounds and process for preparing same
US3305542A (en) * 1965-03-25 1967-02-21 Weyerhaeuser Co Polyethers of levoglucosan

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4362720A (en) * 1977-04-14 1982-12-07 Chembiomed Ltd. Synthesis of 2-amino-2-deoxyglycoses and 2-amino-2-deoxyglycosides from glycals
US4309447A (en) * 1978-09-29 1982-01-05 Kao Soap Co., Ltd. Skin-protecting cosmetic composition
US4870010A (en) * 1984-10-16 1989-09-26 Petroleum Fermentations N.V. Bioemulsified-containing personal core products for topical application to dermopathologic conditions of the skin and scalp
US4999195A (en) * 1984-10-16 1991-03-12 Emulsan Biotechnologies Inc. Personal care products containing bioemulsifiers
US5037969A (en) * 1986-07-03 1991-08-06 Takeda Chemical Industries, Ltd. Glycosyl derivatives and use thereof
US20070249542A1 (en) * 2003-03-24 2007-10-25 Gross Richard A Treatment and prophylaxis of sepsis and septic shock
US7772193B2 (en) * 2003-03-24 2010-08-10 Polytechnic University of NYU Treatment and prophylaxis of sepsis and septic shock
US20100234320A1 (en) * 2009-03-11 2010-09-16 Bioamber Sas Emulsifying compositions based on alkyl polyglycosides and esters
US8492445B2 (en) * 2009-03-11 2013-07-23 Bioamber Sas Emulsifying compositions based on alkyl polyglycosides and esters

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Publication number Publication date
ES477364A1 (es) 1980-10-01
EP0005004A1 (en) 1979-10-31
JPS55303A (en) 1980-01-05
DE2964772D1 (en) 1983-03-24
JPS5623439B2 (es) 1981-05-30
EP0005004B1 (en) 1983-02-16

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